Tetrafluorination of sugars as strategy for enhancing protein-carbohydrate affinity: application to UDP-Galp mutase inhibition

Tetrafluorination of sugars as strategy for enhancing protein-carbohydrate affinity: application to UDP-Galp mutase inhibition

Tetrafluorinated analogues of both UDP-galactosylpyranose and UDP-galactosylfuranose have been synthesized and assayed against UDP-galactopyranose mutase, a key enzyme of M. tuberculosis cell wall biosynthesis. Competition assays and STD-NMR techniques have evidenced not only the first unambiguous c...

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Main Authors: N'Go, Inès (Author), Golten, Samuel (Author), Ardá, Ana (Author), Cañada, Javier (Author), Jiménez-Barbero, Jesús (Author), Linclau, Bruno (Author), Vincent, Stéphane P. (Author)
Format: Article
Language:English
Published: 2014-01-03.
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Summary:Tetrafluorinated analogues of both UDP-galactosylpyranose and UDP-galactosylfuranose have been synthesized and assayed against UDP-galactopyranose mutase, a key enzyme of M. tuberculosis cell wall biosynthesis. Competition assays and STD-NMR techniques have evidenced not only the first unambiguous case of affinity enhancement through local sugar perfluorination, but also showed that tetrafluorination can still have a beneficial effect on binding when monofluorination at the same position does not.

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